Night's Babysitting Adventures
by Kyuro
Summary: What do you get when you mix an extended babysitting adventure, a horny 17-year-old Espeon, and Night the Absol? Let's find out! Rated M for sexual content (Contains femboys & yaoi)! R&R!
1. Chapter 1

**Hello everybody! Kyuro here with another story for you all! So lately I've been thinking about these stories to make that include Shade's counterparts, Light and Night. And thanks to a dear friend of mine, ROTTINGHUMAN, I've been able to accomplish that! This one is involving Night and a femboy Espeon, so yes, it is male on male. Hope you all enjoy it!**

 _ **Disclaimers: I DO NOT OWN POKEMON! Pokemon is a trademark of Nintendo and Game Freak and I take no credit for their work. All OCs in the story belong to either me or ROTTINGHUMAN.**_

 _ **This story contains yaoi (male x male sex), and anthro pokemon. If either one of those rubs you the wrong way, then go ahead and hit that back button.**_

 **Night's Babysitting Adventure**

I grumbled to myself as I came up to the door of the house that had the address that I had gotten. My boss apparently had to take a trip and couldn't bring his son, and asked me if I could babysit for him. I decided to do him a favor this time, because his house was only a few houses down the road from mine and we were old friends from a long time ago. So I got up this morning and grabbed the bag that I had packed the night before and headed over. I didn't have very much details on the matter, as he had to leave on such short notice that he didn't have a chance to explain to me any details other than the fact that their son was an Espeon. Hopefully this is one of those kids that is easy to manage, because while they seem to like me for some reason, I don't have a lot of tolerance towards a lot of their antics.

I knocked on the door and waited for an answer. I heard shuffling around right away, and it almost sounded… frantic. Like they were in the middle of something that I don't really want to imagine a kid doing that would require babysitting. I heard quick, lithe steps pad to the door, and it was only a moment later that the locks clicked and the door opened. On the other side was the Espeon that I was supposed to be watching.

I felt several red flags go off in my head when I first noticed this Espeon. The first one was directed at the fact that this kid looked _way_ older than I expected him to be, definitely a teen. Another was about his build, which was almost completely feminine, with a very full, round ass, flat chest, you can imagine. The third was what he was wearing, which was nothing but a pair of tight jeans. And the fourth was that he was sporting a _very_ noticeable bulge under those jeans, which was the only thing that I saw that proved that this Espeon was a male.

"Hey, so you're Night?" The Espeon asked as he pulled me inside quickly.

"Y-yeah…" I replied, still trying to get over how much of this didn't add up.

"My dad told me you were coming. But he didn't tell me how toned you were…" The femboy continued, beginning to get a bit close to me and rub certain parts of my body. "You seem really strong…"

Was… Was this Espeon teen hitting on me?

"Woah woah woah. Kid settle down." I quickly push his hands down. "That's not how we greet people we've never met. Start with your name."

"S-sorry…" The teen blushed and looked away shyly. "I'm Milo."

I began to feel a stirring in a certain spot in my pants, and I growled to myself. There was no way I was getting aroused by a kid I'm supposed to be babysitting! The son of one of my closest friends no less!

"Okay, well it seems like you know how to take care of yourself for the most part. For that matter, why does your dad feel the need to request that I babysit you?" I asked Milo as I went into the kitchen to get something to drink.

"Maybe because I snuck out once or twice when my parents took long trips like these…?" He replied with this guilty innocence in his voice that made me raise an eyebrow as I poured a glass of water.

"'Snuck out'? How old are you again?" I asked before taking another sip.

"17."

I choked on my water a bit, and responded after a minor coughing fit. "Why the hell am I babysitting a 17 year old?"

"I already told you, I sn-"

"I know, I know. It was rhetorical." I quickly cut him off. It was silent for a while as I walked into the living room to watch tv, with Milo staying closely behind me… almost uncomfortably close. "You know you don't have to be so close to me right?"

"O-Oh sorry…" He stuttered a few more incoherent things before falling silent, but he didn't really let up that much, only falling back by half of a step. I sighed and sat in the middle of the sofa, and Milo quickly took a seat next to me.

"Um, kid, I'm not trying to rude or anything, but I like to have a bit of personal space." I explained, trying to get him to back up a bit. It wasn't a lie either - I don't like people getting this close to me.

"Aww, I just want to get acquaintance with you a bit better. Since we'll be here for a whole month together."

"What?! Your dad didn't tell me that I had to do this for a month!" I had to babysit this kid for a month?! "Although, that would explain why he let me take off work…"

"Yep! We'll be here a whole month, soooo…" Milo slid even closer to me, and now he was attempting to grab my arm again. "What do you like to do?"

I moved my arm away from his reach and slid over a bit. "Nothing specific. I just do what I feel like doing."

Milo slid over again. "Well what do you like doing the most?"

"I'm sure you can figure that one out on your own." I replied, sliding once again. Obviously, I generally choose to keep in shade, so working out is something that I do frequently. He of all pokemon should know that considering how much he's trying to feel me up.

Milo slid over once again. "Hm… I guess I could. It's so obvious." He purred, making me slid over again, but now I was at the end of the sofa. "Well I like to…" He stopped for a bit. "How should I put this? I like to 'have fun' if you know what I mean." He winked.

Oh Arceus help me.

 **And there ya have it folks! The next one is already half way finished, so expect to see it, among other things, coming soon! See you guys later! ~Kyu**

 **Night the Absol © Me (Kyuro)**

 **Milo the Espeon © ROTTINGHUMAN**


	2. Chapter 2

_**Hello again everyone! Kyuro here with chapter 2 of Night's Babysitting Adventure! Sorry it took so long! Enjoy the read~!**_

 _ **Disclaimers: I DO NOT OWN POKEMON! Pokemon is a trademark of Nintendo and Game Freak, and I take no credit for their work. All OCs belong to their respected owners.**_

 **Night's Babysitting Adventure**

"A kid your age shouldn't be into that kind of stuff." We both knew that was a lie, all the kids his age have been looking into that stuff by now.

"I shouldn't be sneaking out when my parents aren't home either, but I guess some rules were made to be broken." This time instead of just sliding next to me, Milo slid all the way over so that he was leaning on me and _really_ beginning to rub himself against me.

His fur mingled with mine and I felt my arousal begin to increase. I had to think fast before I did something that I regret.

"Kid, you're a minor. If we get caught doing something like this, we'll both be in trouble." I warned.

"Who's going to catch us? My parents are going to be gone for a month, or more for all I know, and with them gone it's not like anyone else is going to just walk in here without a key to the house." Milo rebutted, his voice beginning to turn into a whisper as he rested a hand on my chest.

He made a really good point, but I couldn't let my lust get the best of me. So I stood from the sofa a bit quickly, and sighed, adjusting my pants to conceal the bulge that was appearing. "Well I have to go unpack my bag in the guest room and probably go get some extra clothes since I'll be here for so long. You know how to take care of yourself, just don't do anything stupid. I'll get in trouble just as much as you will." I told him without turning around, and without another word, I headed upstairs to the guest room after grabbing my bag. Once I was out of earshot, I sighed loudly.

"That was too close…"

I stepped into the guest room, shut the door, and promptly locked it to make sure that the Espeon downstairs didn't walk in on me. I grabbed my bag and zipped it open, only to go wide-eyed and facepalm. "Got damnit!" I shouted. What are the odds that I grabbed the wrong bag?! To make matters worse, this one was filled with the one thing that I _didn't_ want Milo to see: sex toys. Everything from condoms to riding crops. If that kid saw this, he wouldn't leave me alone for a moment. I had to get this outta here quick.

I quickly zipped up the bag and swung the door open, and standing right in front of it was Milo. "Is everything alright?" He asked. "I heard you shout."

"It's fine. I just grabbed the wrong bag. This one has my workout gear in it." I quickly came up with a lie.

"Oh! Can I see?" Milo asked excitedly, trying to look behind me to see the bag.

"No, I gotta go get the right bag quick, this gear shouldn't be outside of my house." Well, that wasn't a lie.

"Aww pleeeaaaassseeee?" Milo begged. "I promise I won't break-" Milo stopped suddenly with a blush on his face.

"What?"

Milo began to giggle and pointed at the bed. I turned around and lying on the bed was a single dildo from the bag. It must've dropped out without me noticing!

"Got-" I groaned and covered my face with my hand. "Okay, fine, this bag doesn't have clothes in it. So I need to go home and get the right bag. Now can you please-" I stopped as I realized that Milo still had the same expression on his face.

"You okay kid?" A familiar scent hit my nose, but I couldn't pinpoint it. "What's that smell? It smells like…" Then it hit me. I looked down and saw a large bulge in Milo's jeans… along with a wet spot that was slowly getting larger. "Are you…?"

"P-Please… use it on me!" Milo cried out and latched onto me.

"What?" Did I hear that right?

"Please, fuck me with that dildo and anything else that you have in that bag!" Milo repeated, gripping me tightly.

"K-kid, I can't just play with you like that. You're underaged, and I'm not. That's pedo charges for me, a lifetime grounding on you, everything could go wrong if something like this gets out."

"But how's it going to get out~?" He cooed. "Like I said, my parents are going to be gone for who knows how long, and no one's gonna just walk in on us~"

Damn, this Espeon sure was convincing, and he was cute. Wait, no, not cute. He was very…

"Ugh, if I use this on you, will you leave me alone regarding all of this?" I ask, picking up the dildo and showing it to him. He nodded enthusiastically and beamed at me.

 _I can't believe I'm doing this…_ "Well then start undressing."

He reached for the top of his pants before stopping and giving me a nervous look. "Do you promise not to freak out?"

"About what? I'm already at risk for being arrested on pedofilia charges, what do you think could make-" I stopped as Milo pulled his pants off, revealing panties underneath them. "Kid, it'll take a lot more for a guy in panties to freak me out."

"That wasn't what I was talking about…" He replied before beginning to pull his panties down. Then I realized what he was talking about, because when he pulled them off, there were barbs covering the head of his… y'know. Though they closely resemble felines, Espeons are actually canine, so how did he have the cock of a feline?!

"Well that's… very interesting. I thought that Espeons were canines…" I leaned over a bit to get a closer look at the barbs. He was also rather large for a kid his age, and even more so for a feline. It's quite rare that they _ever_ get to his size. "And how big is this? I've never seen one this big."

"They are. I don't know why mines is like this…" Milo explained, before blushing heavily. "I-it was 7 inches last time I checked…"

"That's pretty big for someone your age, a feline no less." I dig around in my bag for the lube.

"Th...Thanks N-Night..." He stammered.

I pulled out the lube and put some in my hand."Alright now get onto all fours." Milo immediately complies and lifts his tail. "This might feel a little bit weird."

 **It begins...**


	3. Chapter 3

_**Hi again everyone! Kyuro's back now, so it's time for the fun to begin~!**_

 _ **Disclaimers: I DO NOT OWN POKEMON! Pokemon is a trademark of Nintendo and Game Freak, and I take no credit for their work. All OCs belong to their respected owners.**_

 **Night's Babysitting Adventure**

Milo shivered as I started rubbing the lube all around his little anal star, whether it was in discomfort or otherwise. Once I felt that it was enough, I poured out some more, this time rubbing it all over the dildo. Once it was also ready, I poked the purple pucker a bit, letting my lust get the best of me and teasing him a bit. Milo whined and started pushing back, desperately trying to get the toy inside him.

"P-please stop t-teasing me!" Every time he pushed back, I pulled the dildo away.

"Then stay still and you'll get it." I ordered with a growl under my breath.

Milo whimpered and remained still. The tips of his tail twitched frequently and his whole body trembled. After a bit more teasing, I gently eased the tip just inside of him and watched as his body visibly shivered and released a relieved moan. When I saw him react like that, I took the liberty of quickly pushing the rest of the 6 incher inside all the way to the hilt.

"A-ah!" Milo gasped and I saw his fur stand on end. "I-I could never get that deep! Night, keep going!"

"You don't pull the strings here, kid." I snapped. "Remember who's doing who a favor, I let you know what it felt like to be filled, and I could just simply pull out right now and leave already…"

Milo looked back with fear in his eyes. "N-no! Please! I'm sorry!"

"Then shut up and enjoy it." I growled again. Once Milo fell silent once more, I pulled the dildo out, leaving only the tip inside, and slammed it all in at once.

Milo howled out, and his hips jerked forward as he started cumming on the carpet. I guess that was all he could take before releasing… how unfortunate-I mean lucky, now I don't have to do anything else. His orgasm lasted for a good 10 seconds before he collapsed in the cum-stained carpet, panting like I just gave him the rutting of his life, which I probably did.

"Nice going, now I gotta clean that up." I sighed.

"S...S-sorry…" He panted. "It was too… too good…"

"Glad you liked it, but now I gotta go put this bag back and go get the bag with my clothes in it." I told him, pulling the dildo out of him, making him shiver a bit and let out another small moan.

I was just about to get out of the door when Milo leapt at me again. "N-no! Please don't leave the toys at home!"

"I didn't plan on it." I replied, prying him off of me. "Since I can't do anything more than that with you, and I'm assuming that that made you want to do even more, I'm going to just leave this bag here so you can have as much fun with it as you like." I explained. _At least he won't keep bothering me about it…_

"Really? Thank you!" He cheered and hugged me a little tighter than I would have liked.

"Y-yeah, now can you let me go so I can go get my stuff?"

"Oh, sure sure!" At once he released me and I made my way out towards the door of the house. Milo followed closely behind me… a little too closely… I'll have to tell his dad about the issues he has with personal space. "Kid, you're a little too close for comfort."

"Oh! Sorry…!" He quickly backed up a few feet, but he looked down and started twiddling his fingers.

I sighed, and mentally shook my head. "What is it kid?"

"C...Can I come with you…?" He asked hesitantly.

Clearly, he was expecting me to scold him, but considering the fact that I literally made him cum all over the floor in my guest bedroom, there really wasn't any harm in it. I _did_ have to babysit him after all. "There's no reason for me to say no really."

"Seriously?" He looked up at me with unnaturally big eyes.

"Yes…" I replied, a bit weirded out by how big he could make his eyes.

"YAY!" He leapt at me again and hugged me around my neck, nearly choking me in the process.

"Okay okay!" I wheezed and quickly started tapping on his arm, indicating that he was choking me.

He giggled and let me go. "I just made you tap out!"

"Whatever, let's get going before it gets too late." I quickly shrugged it off.

Milo quickly dashed off and put some clothes on. The same jeans as before, but with a black shirt. After that, I opened the door and let him out. After Milo stepped out, I closed and locked the door before walking down the driveway and onto the sidewalk. It was getting dark out soon and I didn't want to be walking around with Milo behind me… It might look like I don't have good intentions.

Milo made some very… strange noises behind me as we walked, I don't even really know a good way to describe them. Regardless, I kept walking until we finally made it to my house and I opened the door with a bit of urgency, not wanting anyone nearby to see me taking some teenage kid into my house, much less a cute little Espeon like Milo.

I open the door and walk inside with a bit of urgency, but not enough to make it seem like I was rushing. Milo walked in after me and purred. "It smells so much like you in here Night…" He said. "It's making me get all hot…" I heard him close the door and felt him begin to rub up against my back in a sensual way. "Could you help me cool off~?"

"Kid, I have to get this bag of clothes and get back to your house quickly. I don't have time to play with you." I told him as I began to look around for where I left the bag containing my clothes. Milo whined at my response and followed me around the house. The few times I saw him I could see an obvious bulge in his pants. I growled to myself, hoping that it would go down before I found this bag so that we could leave right away.

Finally, I found the bag where I would normally put the other bag; I must've gotten them mixed up. I grabbed the bag and turned around. "Alright, I have the bag now." Luck must not have been on my side, because that bulge in Milo's pants refused to go down. "... Why are you hard?"

"Well maybe it's because of the big, strong Absol that's babysitting me~" He cooed.

I facepalmed and sighed. "Well you're going to have to do something about that, otherwise we'll have to spend the night here because it'll be too late for us to go back to the house." I explained.

" _I_ can't do anything about it…" Milo purred with a glint in his eyes. "But _you_ can…"

I groan and walk over to the window to see how dark it was outside. "Well it doesn't matter anymore, it's already too dark for us to head home. It took me longer than I thought to find this stupid bag." I explain as I walk over to the couch and lay back. "So it doesn't matter either way."

"Awwww!" Milo whines again and this time straddling me with the bulge in his pants facing me. "Can you pleeeeeaase play with me~?" He begged. "I won't ask again for the rest of the night, I promise!"

I groan, bordering a growl. "You're too hormonal…"

"And you're too sexy." He rebutted, trying to lay down on top of me.

"Slow down there kid, it's getting late, and you're going to need some sleep." I tell him quickly, trying to get him to back off.

"Oh? Do you have plans for tomorrow~?" He giggles and keeps trying to lay down. I put my hands up on his chest to stop him.

"Kid, calm down. Seriously." I say bluntly, pushing him back up into a sitting position and, eventually, off of me completely.

Milo pouted and crossed his arms. "Why don't you want to play with me?!" He whined. "What do I have to do to want you to play with me?!"

I sighed loudly. This Espeon was definitely hormonal; horny one minute, and super upset the next.

"I'll explain it tomorrow. I've had a long day, and I'd like to get some sleep, because I get the feeling tomorrow's gonna be even longer." I explained.

I could see Milo trying to decide what to do next, and for the first time, he nodded and crawled over to the other side of my couch and curled up.

"Okay… Good night…" He whispered, and fell silent.

I sighed to myself and got comfortable. I wasn't lying about what I said, that day had truly been a long one for me, and I was positive that tomorrow was going to be even longer. I looked up at the ceiling and silently asked what did I do to get stuck with a horny Espeon for a month to Arceus above before falling asleep myself.

 **Aww, Night's trying to not have any fun ;-; it's okay, that'll all change in due time... Keep on reading you guys, I'll see you all later! ~Kyuro**


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